1. Carl Lewis "Break It Up" (1987)
Cocky, flamboyant, but most importantly great, Carl Lewis was a legend for his achievements in track and field. His failures as a musician are also legendary, and "Break It Up" stands as his most dubious achievement. There's nothing wrong with a workout/performance montage, but this video is one of the most rancid forms of '80s cheese imaginable. It looks like dude outright stole his swag from Grace Jones (look her up kids).
Unfortunately, Lewis didn't learn from the mistake. In 1993, he attempted to sing the national anthem before an NBA game...with poor results.